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十四元霉素和二氢十四元霉素,由纳什维尔链霉菌MJ885-mF8产生的抗杀鱼巴斯德氏菌的新型抗菌抗生素。II. 结构测定。

Tetrodecamycin and dihydrotetrodecamycin, new antimicrobial antibiotics against Pasteurella piscicida produced by Streptomyces nashvillensis MJ885-mF8. II. Structure determination.

作者信息

Tsuchida T, Iinuma H, Sawa R, Takahashi Y, Nakamura H, Nakamura K T, Sawa T, Naganawa H, Takeuchi T

机构信息

Institute of Microbial Chemistry, Tokyo, Japan.

出版信息

J Antibiot (Tokyo). 1995 Oct;48(10):1110-4. doi: 10.7164/antibiotics.48.1110.

DOI:10.7164/antibiotics.48.1110
PMID:7490216
Abstract

Novel antimicrobial antibiotics against Pasteurella piscicida, tetrodecamycin (1) and weakly active dihydrotetrodecamycin (2) were isolated from a culture broth of Streptomyces nashvillensis MJ885-mF8. The planar structure of 1 was determined to be 2-acyl-4-ylidene tetronic acid alkyl ether containing decaline ring by various NMR spectral data of 1 and its acetyl derivative (3). The structure of 2 was elucidated by comparison with the spectral data of 1 and confirmed by catalytic reduction of 1 into 2. The X-ray crystallography of 2 showed the relative stereochemistry. Their absolute configurations were determined by using modified Mosher's method.

摘要

从纳什维尔链霉菌MJ885-mF8的培养液中分离出了针对杀鱼巴斯德氏菌的新型抗菌抗生素十四元霉素(1)和弱活性二氢十四元霉素(2)。通过1及其乙酰衍生物(3)的各种核磁共振光谱数据,确定1的平面结构为含有十氢萘环的2-酰基-4-亚烷基丁烯二酸烷基醚。通过与1的光谱数据比较阐明了2的结构,并通过将1催化还原为2进行了确认。2的X射线晶体学显示了相对立体化学。使用改良的莫舍尔方法确定了它们的绝对构型。

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